Divot

Derek Andersen

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

  1. #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    6D AGO

    #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    Before becoming one of the most respected early-stage investors in Silicon Valley, Niko Bonatsos was an immigrant from Greece navigating academia, visas, and uncertainty while searching for opportunity in the United States. Over the next 15 years, he became a Managing Director at General Catalyst, investing in iconic companies like Snap and Discord and backing technical founders long before their ideas became obvious to the world. In this conversation, Niko shares what he learned investing through multiple technology cycles and why most successful companies don’t start with the right idea. Niko also reflects on the resurgence of San Francisco as the center of the AI revolution, how ChatGPT reshaped the startup landscape almost overnight, and why this moment feels similar to the early days of social networking and mobile. From recognizing momentum before metrics to investing in overlooked builders, he offers a rare inside look at how early-stage conviction is actually formed. The episode goes deeper into purpose and legacy, exploring immigration, perseverance, parenting, and how Niko measures a life well lived. Rather than chasing status, money, or permanence, he explains why helping deeply obsessed builders bring their dreams to life and empowering others along the way is the mark that truly matters. Follow Niko - X (Twitter): https://x.com/bonatsosFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:42 — Stanford & Silicon Valley: One Intertwined Ecosystem06:18 — Why Founders Keep Chasing the Same Startup Ideas07:37 — Investing Before Consensus: The Real Seed Advantage08:22 — Why Most Successful Companies Don’t Start With the Right Idea09:49 — San Francisco Is Back: The AI Gravity Shift13:24 — Why Niko Invested Early in Snap15:44 — Discord: How a Failed Startup Became a Generational Company18:42 — Talent Is Universal, Opportunity Is Not21:17 — The Signals That Make an Investor Lean In26:49 — Can AI Replace Venture Capitalists?31:30 — The Rise of Tiny Teams and Explosive Growth34:01 — Why Non-AI Companies Are Fighting a Knife Fight38:13 — Leaving General Catalyst: A New Chapter42:18 — Alexander the Great & the Question of Legacy48:19 — “Just Get Started”: The One Idea He’d Give Everyone50:51 — How Niko Measures a Life Well Lived Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#NikoBonatsos #VentureCapital #AI #Startups #SiliconValley #EarlyStageInvesting #Founders #Snap #Discord #GeneralCatalyst #Entrepreneurship #Innovation #DivotPodcast

    54 min
  2. #34: Creativity, Obsession & Building Products That Change the World

    JAN 28

    #34: Creativity, Obsession & Building Products That Change the World

    Before becoming one of the most influential evangelists in the history of technology, Guy Kawasaki was part of Apple’s original Macintosh team, working directly with Steve Jobs during the early days of personal computing. His career has been defined by independent thinking, deep curiosity, and a lifelong commitment to building and evangelizing products that truly matter. In this conversation, Guy reflects on working with Steve Jobs, the difference between mission-driven and ego-driven leadership, and why the best products are built by people solving problems for themselves. He shares hard-earned lessons from Silicon Valley on creativity, obsession, grit, and what it really takes to build things that last. Guy also discusses his role as Chief Evangelist of Canva, the global design platform democratizing creativity for millions worldwide, and how recognizing great products early shaped his journey. From writing 18 books to advising startups and founders, he explains why authenticity consistently outperforms imitation in entrepreneurship and product building. The episode goes deeper into purpose and legacy, exploring learning later in life, embracing setbacks, redefining success, and measuring impact not by status or money, but by one simple idea: empowering people. Follow Guy - Instagram: https://www.instagram.com/guykawasakiFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:1:09 — Starting Surfing at 60: Obsession Beats Talent3:49 — Growing Up in Hawaii: Identity, Culture & Perspective6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom12:44 — Writing 18 Books: Why Most People Shouldn’t Write One16:57 — Build for Yourself: The Origin of Great Products18:20 — Working With Steve Jobs: Mission Over Ego19:40 — Mission-Driven vs Ego-Driven Leadership22:35 — The Halo Effect: Why You Should Be Skeptical of Authority27:22 — Steve Jobs vs Elon Musk: Focus vs Scale30:51 — Don’t Be the Next Steve Jobs. Be the First You33:08 — Finding Your Calling: Loving the Entire “Sandwich”46:31 — Jane Goodall: Purpose Without Retirement52:19 — Guy’s Golden Touch: Finding Gold Early57:24 — Grit as the Real Advantage58:25 — Family, Legacy & Measuring a Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#GuyKawasaki #SteveJobs #ElonMusk #Apple #Canva #Entrepreneurship #Startups #Creativity #ProductBuilding #Leadership #Innovation #SiliconValley #Grit #Purpose #DivotPodcast

    1h 1m
  3. #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    JAN 21

    #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    Before becoming one of the most respected surfboard shapers in the world, Bob Pearson built his craft through obsession, experimentation, and more than six decades of hands-on learning. Since shaping his first board in 1964, Bob has remained committed to one belief: mastery is never finished. Over his career, Bob has shaped more than 100,000 surfboards, becoming a defining force in modern surfboard design and big wave surfing. From his factory in Santa Cruz, California, he has worked closely with legendary surfers including Laird Hamilton, Jay Moriarty, Jamie Mitchell, and others who pushed the limits at waves like Mavericks, Jaws, Waimea, Sunset, and Nazaré. His boards were featured throughout the film Chasing Mavericks, shaping the equipment ridden in the movie. The episode also explores Bob’s friendship with Jay Moriarty, the mindset required for big wave surfing, and the deeper meaning of surfing beyond performance, connection, community, mental health, and joy. At 77 years old, Bob still works nearly every day, driven by curiosity, gratitude, and a lifelong passion for the ocean. Follow Bob - Instagram: https://www.instagram.com/pearsonarrow Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners: Delve Delve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot Pulley Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps: 1:27 — Working 7 Days a Week 2:08 — Shaping 100,000+ Boards 4:54 — Surfboard Design Is Logic 5:38 — Every Board Has Tradeoffs 6:07 — 100+ Ways to Shape a Board 7:07 — From 5ft Boards to Big Wave Guns 7:19 — Why Top Surfers Work With Bob 9:47 — Collaboration Beats Guesswork 11:54 — When Mastery Actually Begins 16:04 — Finding Mavericks Before the Hype 18:14 — Chasing Mavericks & Meeting Jay 25:18 — The Iconic Wipeout Explained 29:56 — Injury, Fear & Healing in the Ocean 38:07 — Bells Beach & Teaching in Australia 40:26 — Surviving Sharks in Big Surf 43:58 — Bali Before Surf Tourism 48:20 — How to Handle Conflict in the Water 55:05 — One Idea for the World 1:01:40 — The Mark Bob Wants to Leave Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast

    1h 3m
  4. #32: Risk, Freedom & Building Billion-Dollar Companies Before the World Believed

    JAN 14

    #32: Risk, Freedom & Building Billion-Dollar Companies Before the World Believed

    Before becoming one of the most influential venture capitalists in Silicon Valley, Tim Draper built a career defined by early conviction, independent thinking, and a willingness to back ideas long before they reached mainstream belief. Over decades, Tim has invested in and supported some of the most transformational companies of the modern era, shaping how the world communicates, moves money, explores space, and builds technology. In this conversation, Tim reflects on backing category-defining companies, including Tesla, SpaceX, Skype, Hotmail, Twitch, and Robinhood, investments that went on to create hundreds of billions of dollars in enterprise value and permanently change global industries. He also shares the impact of Draper University, where thousands of founders have been trained, leading to thousands of companies launched and multiple billion-dollar outcomes. The episode dives deep into Bitcoin and economic freedom, tracing Tim’s early belief in decentralized systems, his experience buying Bitcoin as early as 2011, and why he views it not as a trade but as a long-term technological shift with global implications, especially in a world of inflation, fragile banking systems, and unstable currencies. Follow Tim - X (Twitter): https://x.com/TimDraperFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divot Timestamps:1:50 — Making a Divot: Entrepreneurs, Impact & Building for the Future4:14 — Entrepreneurs Are Superheroes From Day One5:06 — Mindset Beats Talent: Why Entrepreneurship Can Be Taught6:52 — Real Results: Founders Trained, Companies Built, Unicorns Created8:05 — Risk as Identity: When “Crazy” Becomes Your Advantage10:10 — Be Your Own Media Company: Turning Attention Into Power11:56 — Failure Doesn’t Matter: Why Nobody Remembers Your Mistakes13:30 — Boom and Bust: Who Actually Survives Tech Cycles14:24 — The Cost of Inaction: Missing Facebook, Uber & Airbnb17:21 — Buying Bitcoin at $4: Conviction Before Consensus18:55 — Why Bitcoin Survived: The Unbanked, Remittances & Reality20:54 — Predictions vs Regulation: When the Future Gets Delayed25:43 — Bitcoin vs the Dollar: Inflation, Power & Store of Value32:14 — The SVB Wake-Up Call: When Banks Aren’t Safe36:26 — Independent Thinkers Win: Why the 1% Build Everything41:09 — Fixing Broken Systems: Growth, Markets & California48:24 — Raising Independent Humans, Not Followers50:39 — The Core Belief: You Have Your Own Path52:31 — Measuring a Life by Impact, Not Status Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#TimDraper #VentureCapital #Entrepreneurship #Startups #Investing #BillionDollarCompanies #Bitcoin #EconomicFreedom #Innovation #Founders #Leadership #FutureOfTechnology #DivotPodcast

    58 min
  5. #31: How AI Is Transforming Product Building, Leadership, and the Future of Work

    JAN 7

    #31: How AI Is Transforming Product Building, Leadership, and the Future of Work

    In this episode of Divot, we sit down with Aparna Chennapragada, Chief Product Officer for AI at Microsoft, to explore how artificial intelligence is reshaping the way products are built, teams collaborate, and companies scale in an increasingly automated world. Aparna has spent her career at the intersection of technology and human behavior, from leading product at Google and YouTube to shaping Microsoft’s AI strategy today. In this conversation, she shares how the rapid acceleration of AI is compressing years of innovation into months, forcing leaders to rethink how they build, experiment, and make decisions. We discuss what it means to design AI-native products, why traditional development cycles no longer apply, and how the best teams are adapting to constant change. Aparna also reflects on leadership in an era of uncertainty, the importance of curiosity over certainty, and what it takes to build systems that genuinely help people work better. This episode offers a thoughtful look at the future of work, product development, and the mindset required to build responsibly in an AI-driven world. Follow Aparna - X (Twitter): https://x.com/aparnacd Follow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps: 01:44 – “This Time Is Different”: Why AI Adoption Is Unprecedented 02:13 – The Brick Phone Story: How Slow Adoption Used to Be 03:32 – The “Scanned Brochure” Moment: Early Web vs Early AI 04:27 – AI Agents at Work: Prompts as the New PRDs 05:37 – Designers Are Unlocked: Building End-to-End With AI Tools 06:26 – The “Barbell Team”: Model Whisperers + Product Builders 07:31 – How Aparna Stays Ahead: Build Things (No Shortcuts) 09:55 – Thin Steps vs Fat Steps: What Got Easy, What Became the Bottleneck 11:17 – Making AI a “Contact Sport”: Building Reflexive AI Habits 14:33 – Why Startups Win Next: Rethinking Workflows Beats “Just Add AI” 15:54 – The Data Flywheel Problem: Designing for “Learnability” 17:16 – The Next Phase: Products That Improve via UI Reward Signals 17:45 – Small Teams That Ship: Why ~10 People Can Build Fast Now 18:42 – Startup Opportunities: Rewriting the Web for Agents Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

    21 min
  6. #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    12/31/2025

    #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    Josh Reeves, co-founder and CEO of Gusto, shares how he built one of the most trusted platforms for small businesses, and what it truly takes to scale a company with purpose. In this episode, Josh breaks down the realities of building and leading a high-growth startup, navigating regulation, designing products for long-term impact, and maintaining culture as teams and responsibilities scale. He explains how focusing on customers, discipline, and long-term thinking has shaped Gusto’s journey and why sustainable growth matters more than chasing short-term wins. This conversation is a deep dive into founder mindset, leadership, and building enduring companies, essential listening for entrepreneurs, operators, and anyone serious about building something that lasts. Follow Josh - X (Twitter): https://x.com/joshuareevesFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:01:44 – Why Most Startups Fail Before They Even Begin02:27 – The Hidden Cost of Regulation03:48 – Why Payroll and Benefits Matter More Than You Think05:39 – The Real Reason Running a Business Feels So Hard07:44 – The Benefit That Completely Changed Employee Loyalty09:31 – What Sustainable Growth Actually Looks Like11:34 – The Three Metrics That Truly Matter in Business13:58 – Why Chasing Hypergrowth Can Destroy Great Companies15:48 – Building a Company Meant to Last for Decades17:20 – The Leadership Mindset That Separates Great Founders18:54 – Why Being “Busy” Is Not the Same as Making Progress20:21 – How to Identify People Who Will Actually Succeed22:46 – How AI Is Changing the Way Teams Work24:06 – Why Helping Others Is the Ultimate Advantage25:32 – The Life Lessons That Shape Great Leaders27:20 – Gratitude, Perspective, and Staying Grounded29:33 – What Success Really Means (And What It Doesn’t)31:43 – The One Principle That Guides Every Decision33:22 – A Simple Philosophy for a Meaningful Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

    36 min
  7. #29: Survival, Courage & Storytelling - Fire, War & The Brother Who Never Walks Away

    12/17/2025

    #29: Survival, Courage & Storytelling - Fire, War & The Brother Who Never Walks Away

    Before he became an award-winning filmmaker and humanitarian, Brandt Andersen built a tech company from scratch, scaled it to tens of millions in revenue, and sold it before moving into filmmaking, where he went on to produce major films like Everest, Lone Survivor, and American Made. But behind the success is a life shaped by extremes: a skydiving accident that nearly killed him, surviving the Malibu fires with his son, and years spent inside war zones helping people in crisis. In this conversation, Brandt shares the real stories behind I Was a Stranger, his new film inspired by the Syrian refugee crisis. He explains how meeting smugglers, soldiers, parents, and children across Syria, Turkey, Jordan, and Haiti reshaped his understanding of judgment, fear, and humanity. This episode is also deeply personal. Brandt is Derek's older brother. Together, they revisit the moments that forged their bond: childhood chaos, life-or-death situations, and the lessons Brandt passed down through the way he lives. Their conversation reveals the heart, flaws, courage, and philosophy of a man who has spent his life running toward the fire for others, and the profound impact that has had on Derek. Learn More About Brandt - Wikipedia: https://en.wikipedia.org/wiki/Brandt_AndersenFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:1:39 — Who Brandt Andersen Really Is & Why His Story Matters3:03 — The Skydive That Should Have Killed Him8:47 — What Facing Death Taught Brandt About Life14:02 — The Wild Childhood Stories That Shaped Him18:10 — The Banksy Above His Fireplace & His Dark/Light Identity22:30 — From Startup Exit to Hollywood Storytelling28:41 — Producing Everest, Lone Survivor & American Made32:12 — The Real Families Who Inspired I Was a Stranger36:55 — Inside Syria: Crisis Through Human Eyes41:38 — “Don't Judge People by Their Worst Day”45:52 — Haiti Earthquake: Chaos, Hunger & Purpose52:10 — The Moment That Changed His View of Humanity1:12:03 — Trapped in the Malibu Fires With His Son1:29:45 — What Brandt Ultimately Wants People to Understand Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#BrandtAndersen #IWasAStranger #Filmmaking #Storytelling #SyrianRefugeeCrisis #HumanitarianAid #WarZones #Resilience #Courage #PurposeDrivenLife #LoneSurvivor #Everest #AmericanMade #Leadership #PersonalGrowth #DivotPodcast

    1h 32m
  8. #28: Reinvention & Resilience - Faith, Failure & Becoming Who You Are Meant to Be

    12/10/2025

    #28: Reinvention & Resilience - Faith, Failure & Becoming Who You Are Meant to Be

    Before he became chairman of the Napoleon Hill Institute, David Meltzer lived a life driven by scarcity, ambition, and the need to prove himself. Raised by a single mother in Akron, he chased success to change their future, eventually becoming a multimillionaire and CEO in the sports world. But behind the achievements was an identity built on ego, bad habits, and external validation, leading to the breaking point that forced him to confront who he’d become. In this conversation, David shares the mindset shift that saved his marriage, the four values that rebuilt his identity, and how losing over $100M became the foundation for a healthier, more purposeful life. He explains how faith, gratitude, sleep discipline, and time mastery helped him recover, along with the frameworks he teaches today to serve his mission of empowering over a billion people. From stop-drop-and-roll to emotional chemistry and using failure as fuel, David breaks down the tools that rebuilt his life from the inside out. A vulnerable and practical look at reinvention, this episode reveals what it truly takes to grow through loss and rebuild meaning. If you’re navigating change, recovering from setbacks, or redefining success, David’s story offers perspective, resilience, and a blueprint for living with intention. Follow David - X (Twitter): https://x.com/davidmeltzerFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 — David’s Life: The Fall That Saved Him2:21 — Akron Roots: Scarcity, Survival & a Single Mom Who Never Quit4:58 — The Dream Life That Almost Destroyed Him7:06 — His Wife’s Warning: The Sentence That Changed Everything8:44 — Rebuilding the Man: The Four Values That Brought Him Back10:51 — Losing $100M: The Collapse He Was Finally Prepared For13:02 — The Habits That Saved His Marriage, Mind & Future17:47 — Failing Faster: Why Losing Is the Only Way to Win22:06 — Emotional Alchemy: Training His Reactions Every Single Day29:32 — “Stop, Drop & Roll”: The Method That Resets His Entire Life34:39 — Ego, Pain & Perspective: Understanding the Chemistry of a Breakdown42:18 — Turning Trauma Into Purpose: How He Rewrote His Story53:17 — The One Lesson He Wants to Leave Humanity55:38 — “What I Hope God Says to Me When I Arrive” Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DavidMeltzer #Reinvention #Resilience #Mindset #LifeLessons #PersonalGrowth #SelfImprovement #OvercomingFailure #EmotionalIntelligence #SpiritualGrowth #Leadership #DivotPodcast

    57 min
4.9
out of 5
19 Ratings

About

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

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